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Cheap flights from New York to Chicago from $99

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 19/4. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
8 Mar — 15 Mar1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from New York to Chicago are usually found in February or January, booked 81 days in advance, depart on a Tuesday or Friday and return on a Thursday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 6 February 2026.

Fri 6/323:05
EWR
-
ORD
Nonstop2h 35m
Spirit Airlines
Sun 8/318:51
ORD
-
EWR
Nonstop2h 09m
Spirit Airlines
Deal found 4/2$126
Sun 22/223:05
EWR
-
ORD
Nonstop2h 35m
Spirit Airlines
Sun 1/318:51
ORD
-
EWR
Nonstop2h 09m
Spirit Airlines
Deal found 6/2$129
Mon 2/323:05
EWR
-
ORD
Nonstop2h 35m
Spirit Airlines
Fri 6/320:16
ORD
-
EWR
1 stop13h 41m
Spirit Airlines
Deal found 4/2$131
Sun 22/223:05
EWR
-
ORD
Nonstop2h 35m
Spirit Airlines
Mon 23/218:51
ORD
-
EWR
Nonstop2h 09m
Spirit Airlines
Deal found 5/2$141
Tue 17/308:02
EWR
-
ORD
1 stop12h 49m
Spirit Airlines
Tue 24/318:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Deal found 6/2$144
Sat 21/322:54
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Sat 28/318:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Deal found 4/2$145
Mon 23/310:06
EWR
-
ORD
1 stop10h 57m
Spirit Airlines
Sun 29/318:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Deal found 5/2$146
Tue 7/422:54
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Mon 13/418:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Deal found 3/2$149
Sat 7/323:05
EWR
-
ORD
Nonstop2h 35m
Spirit Airlines
Sun 8/318:51
ORD
-
EWR
Nonstop2h 09m
Spirit Airlines
Deal found 6/2$151
Wed 4/310:05
EWR
-
ORD
1 stop8h 41m
Spirit Airlines
Sun 8/318:51
ORD
-
EWR
Nonstop2h 09m
Spirit Airlines
Deal found 4/2$154
Sat 7/312:02
EWR
-
ORD
1 stop8h 09m
Spirit Airlines
Sat 14/318:01
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Deal found 5/2$161
Thu 19/223:05
EWR
-
ORD
Nonstop2h 35m
Spirit Airlines
Sun 22/218:51
ORD
-
EWR
Nonstop2h 09m
Spirit Airlines
Deal found 4/2$162

Find flight deals from New York to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 6 February 2026.

Round-trip from

$126

One-way from

$85

Popular in

August

Cheapest in

February

Average price

$267

Good one-way deal

$248 or less
Spirit Airlines
  • Spirit Airlines
  • 6/3-8/3
  • Nonstop
  • 4h 44m total
  • New York to Chicago
Search Deals
Spirit Airlines
  • Spirit Airlines
  • 20/4
  • Nonstop
  • 2h 38m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average return price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 6 February 2026.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

New York

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 7/3

12:02-19:11

1 stop8h 09m

Chicago O'Hare Intl

Sun 8/3

18:51-22:00

Nonstop2h 09m

$188

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 28/2

12:02-21:13

1 stop10h 11m

Chicago O'Hare Intl

Sun 1/3

18:51-22:00

Nonstop2h 09m

$188

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 18/2

23:05-00:40

Nonstop2h 35m

Chicago O'Hare Intl

Fri 20/2

18:51-22:00

Nonstop2h 09m

$192

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 27/5

07:00-08:42

Nonstop2h 42m

Chicago O'Hare Intl

Thu 28/5

07:15-10:35

Nonstop2h 20m

$197

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 1/5

21:50-23:37

Nonstop2h 47m

Chicago O'Hare Intl

Sun 3/5

06:00-09:12

Nonstop2h 12m

$197

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 9/5

14:36-16:17

Nonstop2h 41m

Chicago O'Hare Intl

Mon 11/5

21:55-01:15

Nonstop2h 20m

$197

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 5/5

07:30-09:14

Nonstop2h 44m

Chicago O'Hare Intl

Thu 28/5

07:15-10:35

Nonstop2h 20m

$197

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 27/2

15:17-17:00

Nonstop2h 43m

Chicago O'Hare Intl

Sun 1/3

06:00-09:07

Nonstop2h 07m

$211

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 6/3

19:45-21:34

Nonstop2h 49m

Chicago O'Hare Intl

Wed 11/3

21:23-00:28

Nonstop2h 05m

$211

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 23/4

09:00-10:44

Nonstop2h 44m

Chicago O'Hare Intl

Sun 26/4

07:00-10:20

Nonstop2h 20m

$224

Flights are sorted by cheapest return flights first.

Deals found on 4/2

Showing 1-10 of 23 results
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Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

How far ahead should I book a flight from New York to Chicago?

Use this chart to determine the optimal time to book a return flight from New York to Chicago. Price data was last updated on 30 January 2026.

The best time to book flights from New York to Chicago is 81 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from New York to Chicago?

Currently, December is the cheapest month in which you can book a flight from New York to Chicago (average of $69). Flying from New York to Chicago in July is currently the most expensive (average of $171). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NYC to CHI?

Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 6 February 2026.

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 85% versus a flight at midday.

Weekly flight availability from New York to Chicago

Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 6 February 2026.

The most flights from NYC to CHI are scheduled on a Friday (181 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 on average).

How much does it cost for a return flight from New York to Chicago?

How often are flights from New York to Chicago delayed?

About 18% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 158 minutes.

What is the most punctual flight time for New York to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on New York to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

Related info for your journey

Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New York to Chicago?

    Airlines like Spirit Airlines and United Airlines fly from New York to Chicago in about 2h 35m. The time it takes to get you to your destination is usually consistent. New York and Chicago are separated by a distance of 1152 km. Generally, flights for this route are direct.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: SAUDIA (75%), WestJet (74%), Endeavor Airlines (71%).

  • What are the cheapest flights from New York to Chicago?

    The cheapest flight price from New York to Chicago is $248. On average you can expect to pay $306. The most popular route, (Newark - Chicago O'Hare Intl), can usually be booked for $85.

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York to Chicago?

    Currently, December is the cheapest month in which you can book a flight from New York to Chicago (average of $69). Flying from New York to Chicago in July is currently the most expensive (average of $171). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for New York to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from New York to Chicago?

Cheapflights makes it easy to find New York to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Cheapflights helps you find that perfect flight to Chicago from New York by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from New York to Chicago with no change fees?

Yes, we can. To see specific flights from New York to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

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